19714-18-2Relevant articles and documents
Antiproliferative activity of novel isatinyl/indanyl nitrones (INs) as potential spin trapping agents of free radical intermediates
Maiuolo, Loredana,Feriotto, Giordana,Algieri, Vincenzo,Nardi, Monica,Russo, Beatrice,Di Gioia, Maria Luisa,Furia, Emilia,Tallarida, Matteo Antonio,Mischiati, Carlo,De Nino, Antonio
, p. 299 - 304 (2018)
A series of ketonitrones derived from isatin and indanone (INs) were synthesized and evaluated for their antiproliferative activities against several human cancer cell lines. Then, the antioxidant properties of these substrates were measured by the DPPH test to report their biological activity in terms of their spin trapping action. In particular, one substrate has showed very high biological and scavenging activity, probably due to the strong correlation between its spin trapping activity and structure.
One-pot solvent free, green route to novel substituted spiro[oxindole-isoxazolidine] derivatives: novel candidates as antimicrobial agents
KAUR, MANPREET,BHATIA, SUMEET KAUR,SINGH, BALDEV
, p. 1299 - 1303 (2021/06/09)
The environmentally benign catalyst and solvent-free synthesis of ketonitrones may not always be accomplished by simple condensation reactions. The occasional reports of green synthetic routes toward these compounds have been reported. The key features of
Single-Step Approach toward Nitrones via Pyridinium Ylides: The DMAP-Catalyzed Reaction of Benzyl Halides with Nitrosoarenes
Jung, Yeonghun,Hong, Jee Eun,Kwak, Jae-Hwan,Park, Yohan
, p. 6343 - 6350 (2021/05/29)
A single-step approach is reported for the preparation of nitrones from benzyl halides and nitrosoarenes via pyridinium ylides, utilizing 4-dimethylaminopyridine (DMAP) catalyst and mild reaction conditions (Li2CO3, dimethylacetamide, and room temperature). The reaction provides both keto-and aldonitrones in high yields with a wide scope for benzyl halides and nitrosoarenes. In the same reaction system, 2-methyl-2-nitrosopropane, which does not have an aryl group, also affords the corresponding N-tert-butyl nitrones from primary benzyl bromides that have an electron-withdrawing group. As an application of the reaction, methyl 2-bromo-2-phenylacetate was used to prepare the corresponding isoxazolidine by a sequential one-pot synthesis.
Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones
Mo, Xue-Ling,Chen, Chun-Hua,Liang, Cui,Mo, Dong-Liang
, p. 150 - 159 (2017/11/28)
A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.
Synthesis and Evaluation of Novel Spiro[oxindole-isoxazolidine] Derivatives as Potent Antioxidants
Kaur, Manpreet,Singh, Baldev,Singh, Baljit,Arjuna, Anania
, p. 1348 - 1354 (2017/03/27)
The antioxidant activity of isatin derivatives can be described with the presence of enolic hydroxyl group at the second position of the ring because of the keto-enol tautomerism between NH and C O groups of indolone moiety. The reducing ability of the tested compounds was evaluated by their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) at various concentrations. Novel spiro[oxindole-isoxazolidine] derivatives (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i) have been synthesized by 1,3-dipolar cycloaddition reactions of variously substituted maleimides (1) with isatin ketonitrone (3) and tested for their in vitro antioxidant potency in the DPPH assay. All the synthesized compounds have been identified as potent in vitro antioxidants.
Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: Solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
Maiuolo, Loredana,Merino, Pedro,Algieri, Vincenzo,Nardi, Monica,Di Gioia, Maria Luisa,Russo, Beatrice,Delso, Ignacio,Tallarida, Matteo Antonio,De Nino, Antonio
, p. 48980 - 48988 (2017/11/06)
The spiro-oxindoles have found wide application because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding and stereoselective. Then, we explored the possibility to synthesize nucleobase-containing spiro-isoxazolidines with isatin and indanone nuclei by solvent-free MW-assisted 1,3-dipolar cycloaddition, obtaining good results in yields (74-85%), and regio- and diastereoselectivity. Theoretical calculations were done to analyze the difference of reactivity of isatin and indanone derivatives with hydroxylamines.
Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process
Wu, Si-Yi,Ma, Xiao-Pan,Liang, Cui,Mo, Dong-Liang
, p. 3232 - 3238 (2017/03/23)
An efficient selective N-arylation of 3-(hydroxyimino)indolin-2-ones with diaryliodonium salts to prepare (Z)-N-aryl oxindole nitrones has been achieved under simple base-mediated conditions. The reaction tolerated a variety of diaryliodonium salts with diverse and sensitive functional groups. Studies on the oxime structures revealed that the pyrroline ring and carbonyl group in 3-(hydroxyimino)indolin-2-ones played important roles in the selective N-arylation process. The N-aryl oxindole nitrones could be prepared rapidly and easily at the gram scale.
Yb(NTf2)3-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes to construct novel spiro[tetrahydro-1,2- oxazine]oxindoles
Yang, Hai-Bin,Shi, Min
supporting information, p. 8236 - 8243 (2012/11/07)
Yb(NTf2)3-catalyzed [3 + 3] cycloaddition between isatin ketonitrones and cyclopropanes is described. A variety of spiro[tetrahydro-1,2-oxazine]oxindoles were obtained in moderate to good yields along with good regioselectivities. This is the first example of the intermolecular [3 + 3] cycloaddition between ketone-derived nitrones and cyclopropanes. The Royal Society of Chemistry 2012.
